@Maxperson,
@UngainlyTitan,
@Fanaelialae,
@Micah Sweet,
@Flamestrike,
@FrozenNorth, etal.
Can a compromise be helpful? I am probably ok with:
• A Downtime of at least a week of rest automatically counts as a long rest.
• During an adventure, all rests are short rests.
• Twice before the next level, a player can change one short rest into a long rest.
This ability to switch a short rest satisfies my need for narrative flexibility to be able to tell different kinds of adventure stories, when combats happen at different frequencies, whether covert ops surprise-attacking room to room or pirates sailing the open seas.
When characters end an adventure and go into Downtime, they automatically refresh: even if they used up their long rests and havent leveled up yet. A minimum of a week of rest defines a Downtime, to ensure the flavor that the players are definitely not adventuring. (Also, a brief google found that eight days is the average amount of ideal vacationing for the purpose of relaxing from work. So about a week Monday to Monday off, makes sense.)
There are still ambiguous corner cases. In my campaigns, players normally do social encounters during Downtime, relevant to the various ambitions they are working toward. So it is possible to level up during Downtime. This shouldnt be a problem.
More awkwardly, a seafaring campaign might sail for months. Encounters might be weeks apart. So whether a sailor on a vessel is in an adventure or in a Downtime is ambiguous. Maybe, if the player hasnt seen combat action for a week, the journey can start counting as a downtime? Then the second week is a week of Downtime that automatically counts as a longrest? Like I said, awkward.
Anyway, the extensive timeframe of journeys can be handled separately. The point is, a Downtime automatically refreshes regardless of leveling. Meanwhile, adventures have to long rests per level and the player decides when these two happen.